The present invention relates to 2-acyl-5-substituted thiatetrahydrofuran-4-ones produced by the novel process of our invention and novel compositions using one or more of such 2-acyl-5-substituted thiatetrahydrofuran-4-ones or "cis" or "trans" isomers thereof to alter, modify, augment or enhance the flavor and/or aroma of consumable materials or impart flavor and/or aroma to such consumable materials.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) flavors to (or in) various consumable materials. These substances are used to diminish the use of natural products, some of which may be in short supply and to provide more uniform properties in the finished product. Coffee-like, roasted, cocoa-like, caramel-like, licorice and roasted almond aroma and flavor characteristics are particularly desirable for many uses in foodstuff flavors, chewing gum flavors, toothpaste flavors and medicinal product flavors. Sweet, caramel/coffee aromas and flavors prior to smoking and sweet, caramel/coffee, nutty/pyrazine and roasted nutty aroma and taste characteristics on smoking are particularly desirable in tobaccos as well as tobacco flavoring compositions and in tobacco substitutes and flavoring compositions for such tobacco substitutes.
When one mole of diacetyl is reacted with one mole of furfuryl mercaptan, a coffee flavored reaction product is produced which has been found to contain a small percentage (about 10% by weight) of 5-acetyl-2-(furfurylthio)dihydro-2,5-dimethyl-3-[2H]furanone with 1 mole of the "cis"-"trans" isomers in a ratio to the other of the "cis-"trans" isomers of about 2:1. The process for preparing such a reaction product (without describing the constituents of the products) is set forth in Swiss Pat. No. 128,720 published on Nov. 16, 1928. It is stated in the Example at Column 2 on page 1 thereof that when one mixes furfuryl-2-mercaptan and diacetyl, the product (alpha-oxy-alpha-acetylethyl)furfuryl-2-sulfide is produced.
U.S. Pat. No. 1,696,419 issued on Dec. 25, 1928 (Title: "Method of Producing Artificial Coffee Aroma") discloses the production of a coffee flavor using:
"One part of diacetyl, four parts of acetyl propionyl, four parts of methyl ethyl acetaldehyde, three parts of acetaldehyde, two parts of alpha methyl furfural, one part of furfural, three parts of pyridine, two parts of isovaleric acid, one part of phenol, one part of isoeugenol, 0.5 parts of guiacol, 0.5 parts of alpha methyl cyclopentenolone, 0.6 parts of methyl mercaptan, 0.3 parts of furfuryl mercaptan, 0.3 parts of n-octyl alcohol and 0.4 parts of thioguiacol"
At page 3, column 1, lines 29-39.
No member of the genus of compounds having the structure: ##STR1## (wherein R.sub.1, R.sub.2, R.sub.1 ', R.sub.2 ' and R.sub.3 are defined above) is indicated to be produced as a result of admixing at higher temperatures the foregoing ingredients.
Canadian Pat. No. 1,002,383 issued on Dec. 28, 1976 discloses the preparation of a popcorn-type flavor by reacting glyoxal (an alpha, beta-dicarbonyl compound) with a "sulfide source" at elevated temperatures. The resulting material is indicated to have advantageous properties over reaction products of "sulfide sources" with such materials as 2,3-pentane dione, which is indicated on page 8 to give rise to a product having a "burnt character" when it is reacted with a "sulfide source". Organic "sulfide sources" are also mentioned in Canadian Pat. No. 1,002,383, but are only exemplified by 1-cysteine.
Thus, nothing in the prior art discloses either explicitly or implicitly any member of the genus of the compounds having the structure: ##STR2## wherein R.sub.1, R.sub.2, R.sub.1 ' and R.sub.2 ' are the same or different and each represents hydrogen or methyl and wherein R.sub.3 represents one of C.sub.1 -C.sub.9 alkyl, benzyl, phenyl, substituted or unsubstituted allyl having the structure: ##STR3## substituted or unsubstituted 3-furyl having the structure: ##STR4## (wherein R.sub.4 and R.sub.8 are the same or different and each represents hydrogen or methyl), hydroxyalkyl, oxoalkyl, hydroxycycloalkyl or oxocycloalkyl having the structure: ##STR5## (wherein R.sub.5 and R.sub.6, taken separately, represents hydrogen or C.sub.1 -C.sub.3 alkyl or R.sub.5 and R.sub.6, taken together, complete a cycloalkyl group) and wherein Q is one of the moieties: ##STR6## prepared according to the process of dimerizing one or more alpha, beta-alkane dione(s) to form one or more alpha, beta-alkane dione dimer(s) having the structure: ##STR7## and reacting the said alkane dione dimer(s) in acidic medium and in the presence of a solvent with a mercaptan having the structure: EQU R.sub.3 SH